Tuscany

September in Tuscany is the revelation that changes how you think about the region. The vendemmia (grape harvest) is underway in the Chianti and Montalcino hills, the light softens to gold in the afternoons, and the summer crowds have thinned enough that you can actually move through places without elbowing past tour groups. The cypress-lined roads look exactly as you imagined them when you decided to go to Italy. The hotels and agriturismos that were booked solid in August suddenly have availability. This is Tuscany at its least stressful and most genuine.

Florence is where most people spend their time, but the Oltrarno neighbourhood on the south bank of the Arno is where the real city lives. The Pitti Palace and its gardens, the leather workshops on Via de’ Bardi (where craftspeople are still making leather as they did in the Renaissance), the cicchetti culture in wine bars—this is the side of Florence that doesn’t appear in the guidebook photos. The Brancacci Chapel in Santa Maria del Carmine holds Masaccio’s frescoes, some of the most important paintings in Western art, and entry is limited to 30 people at a time. You’ll stand in front of them without fighting through crowds. If you arrive at Siena at 7am, before the tour buses, the Piazza del Campo is one of the great Italian experiences: the medieval herringbone brick in the piazza, the nine sections representing the medieval governance, the Palazzo Pubblico at the wide end. The Palio horse race (July and August) is genuinely extraordinary but requires booking accommodation months ahead.

The Val d’Orcia south of Siena is where the landscape becomes almost abstract. Pienza is the ideal Renaissance city, built in a single century as a utopian vision; you can walk from one end to the other in a day and grasp its entire design. Monticchiello is a fortified village on a ridge overlooking hills that roll to the horizon. La Foce gardens (open Wednesday afternoons and select dates) were designed by Iris Origo; the cypress avenue that lines the garden drive is iconic and appears in a thousand photographs of Tuscany. The Chianti Classica route between Greve in Chianti and Castelnuovo Berardenga passes through Panzano (where Dario Cecchini runs one of Italy’s legendary butcher shops and serves 10-course tastings of beef), Radda, and Gaiole. Montepulciano climbs uphill to the Piazza Grande; Montalcino sits below its fortress and produces Brunello, possibly Italy’s finest wines.

The food is inseparable from the landscape. Bistecca alla Fiorentina is a Chianina beef T-bone ordered al sangue and priced by weight; never ask for it well done. Ribollita is twice-cooked bread soup with cavolo nero (Tuscan kale), and pici are hand-rolled thick spaghetti from the southern part of the region. Cinghiale (wild boar) becomes pasta, roasted, or cured. Pecorino di Pienza is a sheep’s cheese that melts on your tongue. Cantucci (almond biscuits) and Vin Santo are the traditional dessert. The olive oil from around Lucca or the Chianti hills is green, peppery, and nothing like the commodity olive oil you buy at home. September is harvest time, and if you visit a winery or olive mill you’ll see the year’s work coming in. Montalcino and Montepulciano wines are serious things; a basic Brunello or Vino Nobile costs more than expected, but the quality justifies it.

May and June are perfect if you prefer not to visit in September, though accommodation is more expensive. October is beautiful but starts to get cool in the evenings. Avoid August entirely if you can; it’s hot, crowded, and many restaurants close in the second half of the month. Book the famous restaurants (Dario Cecchini, Enoteca Pinchiorri in Florence) well ahead. The Wine Road and the Val d’Orcia are best explored by car; the distances are short but the back roads reward driving. Hire a driver for a day if you want to do serious wine tasting without worrying about driving.

Tuscany rewards both first-timers and those returning. Even if you’ve been to Florence and Chianti before, the Val d’Orcia and the hill towns south of Siena offer a completely different Tuscany—less wine tourism, more genuine landscape and art. Seven to ten days is the minimum to move beyond the obvious places.